School Sissy Stories

109,522 results
Orientation
Length
Source
Infinite Scroll

Big U Pride Ch. 03: The Squad Forms

by latinarita4 on Jul 27, 2020
Transgender & Crossdressers

Remember to check on parts 1 and 2 before you read this! Also, please rate and review my stories! I love hearing feedback from readers! If you have suggestions, just send them right along! Maybe your suggestion will be featured in a future chapter... ________________ Most days at the campus health center were typically light affairs. Usually it's the rout...

Black Mistresses For Black Sissy

by Samuelx on Aug 18, 2017
Fetish

A lot of Black women in the world of BDSM consider themselves dominant, which is fine, but they seem to cater exclusively to White male submissive types. I take my clients anyway they come, since I am a professional dominatrix. I do enjoy playing with Black men, though. Unlike White subs, the brothers always make you work for it. My name is Shana Drummond an...

Truth or Dare Sissy

by maxy007 on Sep 12, 2017
Transsexuals & Crossdressers

It was your usual high school gath. At the time I was just an innocent 18 year old enjoying life with some friends. My name is max, and this is the story of how a small 20 person gathering turned me into a sissy. It was mid-year of the final year of high school, and my friend Isabel was holding a gath on Saturday night. It was a welcome break from study, a...

Alt. Queen of the Left-hand Turns

by maxdname on Sep 16, 2017
Romance

See that beautiful girl in the poster? When I first met her she was a simple hillbilly girl from Appalachia sleeping with stock car drivers in order to get a pit pass. Look at her now: she's a blond and a model with her own TV show that earns her more in a year than most stock car drivers will earn in a lifetime on the circuit. A national racing magazine i...

Danni

by Coder3445 on Jan 6, 2020
Transgender & Crossdressers

This story is a complete work of fiction. In said work all characters are at least 18 years if age. This is my first story so constructive criticism is welcomed. Enjoy or not don't let me tell you what to do. *** Daniel had an issue, the issue being that when he had first started watching porn he like any other cis-gendered male had started with a voluptu...

The Making of Davina Ch. 01

by Timewarp10 on Oct 31, 2018
Transgender & Crossdressers

It was 1966, England had won the World Cup! The swinging sixties were in full swing. David had started working in the sale's office of Telford Safety Engineering Ltd. He held the grand title of Assistant to the Sales Manager, which meant in reality he was the office boy; he ran errands and made the tea. At eighteen, it wasn't his first job. Since leaving sch...

Sammi Meets Teddy

by Sissy_Sammi_ on Dec 8, 2017
Transsexuals & Crossdressers

Ever since Sammi was born Sam had been working his ass off, both in pants and panties. His grades in school improved rapidly as his outlook on life improved, and before he knew it he had sent away college applications and received acceptance letters. He knew where he was going to college, and before he knew it he was graduating. The rest of the year coasted...

Sara's Amazing Night

by Sexy_SaraCD on Sep 16, 2017
Transsexuals & Crossdressers

I felt his entire weight, his entire body push me against the wall and the more I struggled the harder he pushed into me. My hands are firmly planted on the wall and my eyes are closed. At this moment, I feel panic. Panic of what may come soon. His leg, strong and thick, push my legs apart but my tight skirt stops them. He doesn't let that prevent him from...

How I Became a Sissy for BBC

by Caged4goddessd on Mar 12, 2019
Transgender & Crossdressers

It really all started in college. I was a fairly typical and somewhat popular guy. I was involved in a few different clubs and a member of a popular fraternity on campus. Of course, this led to me knowing quite a few of my classmates and at the time I had my share of success with the females in my classes. It was my junior year and at the time I was dating...

Chuck

by wajawhiii on Jun 5, 2018
Erotic Couplings

My name is Marjerie. I'm thirty-nine years old. I was married to George when I was only twenty. He left when I was just twenty-three and Charles was only two. I got an uncontested divorce three years after he disappeared. Charles is the only thing George gave me and the best thing I've ever received. Charles is now eighteen and just graduated from high scho...